1,5(and 1,8)-dihydroxy-8(and 5)-nitro-4-nitroanilino-anthraquinones



United States Patent US. Cl. 260380 2 Claims ABSTRACT OF THE DISCLOSURE Dyestuffs having the formula:

wherein X is selected from the group consisting of hydrogen and NO and Y and Z, each being different from the other, and selected from the group consisting of OH and NO have been found to be particularly suitable for dyeing polyester materials.

This application is a continuation of my copending application Ser. No. 283,524, filed May 27, 1963, now abondoned.

The present invention relates to a new class of dyestuffs suitable for dyeing various materials and particularly for dyeing polyester materials. The invention further relates to a novel dyeing process.

I 'have surprisingly found that compounds of the general formula wherein X is selected from the group consisting of hydrogen and NO and wherein Y and Z are difierent from one another and are each selected from the group consisting of OH and NO dye, preferably under pressure at a temperature between 110 and 130 C., polyester, particularly polyethylene terephthalate, materials, e.g., fibers, films and other manufactured articles, to a blue-reddish shade exhibiting unusual fastness to sublimation, light, and to the action of trichloroethylene.

Compounds defined by the above general formula may be obtained by condensing a dinitrodihydroxyanthraquinoue and, respectively, a mono or dinitroaniline.

The condensation is carried out using a high boiling solvent, preferably nitrobenzene or a-chloronaphthalene, at a temperature of from about 130 to 210 C., and preferably from about 160 to 210 C.

The molar ratio between the dinitrodihydroxyanthraquinoue and the nitroaniline is preferably from about 1:2 to 1:5

The following examples will further illustrate this invention. All parts are by weight unless otherwise stated.

Example 1 3.3 g. of dinitrochrysazin are heated for 8 hours at 180 C. together with 5.5 g. of metanitroaniline and 20.0 g. nitrobenzene. After cooling, the mass is filtered, washed with minor amounts of C H OH, and the cake is then steam distilled in the presence of 0.5 g. Na CO The product is washed until a neutral reaction is obtained, and then is filtered and dried, which product is the metamononitroanilide derivative. The foregoing product is used to dye (under pressure, at a temperature of from about to C.) polyethylene-terephthalate to obtain a blue shade having outstanding fastness and resistance to sublimation, light, and to the action of trichloroethylene.

Example 2 Example 3 By proceeding as described in the foregoing examples, but using a corresponding amount of a-chloronaphthalene instead of nitrobenzene and carrying out the condensation at a temperature of about -200" C., the same dyestutf is obtained.

Having thus described the invention, what is desired to be secured and claimed by Letters Patent is:

1. A dyestuif having the formula:

I l Z -Q wherein X is selected from the group consisting of hydrogen and NO and Y and Z, each being different from the other, are selected from the group consisting of OH and NO;.

2. The dyestufi' of claim 1 having the formula:

OH OH I H N02 0 NH References Cited FOREIGN PATENTS 1,001,784 1/1957 Germany.

LORRAINE A. WEINBERGER, Primary Examiner. HAROLD C. WEGNER, Assistant Examiner.

US. Cl. X.R. 8-39 

